Chosen By: Amie O’Shaughnessy, founder and CEO of Ciao Bambino. After having her son, Amie searched extensively for credible resources to provide family-focused advice, direction and useful accommodation information. She quickly realized that there were no relevant resources available, particularly for a discerning traveler, so she decided to help solve this problem and started Ciao Bambino.

Looking for something a little more luxurious? No problem. Check out our lists of the best hotels by island. If money is not so much the issue, we recommend Montage Kapalua Bay on Maui and Mauna Kea Resort on the Big Island. Both of these five star resorts are cozied up to beaches that have been voted #1 Beach in America by Dr. Beach. In addition, Montage Kapalua Bay is Hawaii’s newest Forbes Five Star property. Another bonus? They both usually offer specials along the lines of “get the 4th night free.”

When the lure of a tropical paradise beckons, the Caribbean is second to none. Immerse yourself in the laid-back island lifestyle, and enjoy wonderful all-inclusive resorts, fantastic beaches, marvelous diving and snorkeling, challenging golf and great shopping. Whether you are looking for the perfect atmosphere for a romantic getaway or an exciting adventure for the whole family, Caribbean vacations are fun for everyone.

From the blue waters and white sands of Mismaloya to the secluded shores and jade backdrop of Majahuitas, it would be easy to call Puerto Vallarta heaven on earth. But aside from its stunning beaches and natural landscapes, Puerto Vallarta has plenty more for budget travelers. Cruise the Rio Cuale Riverwalk, or tackle a challenging hike through the El Tuito jungle to reach the amazing Yelapa Waterfall.

Why: Santa Fe is a creative vortex that thrives at 7,200 feet, at the foothills of the Sangre de Cristo Mountains, attracting artists and healers from around the world. It’s an ideal getaway for nature lovers, art enthusiasts and spa seekers. Surrounded by natural beauty, the city’s roots go deep with a Native American, Hispanic and Anglo heritage. This year, the city is 407 years old and is the oldest capital city in the United States. It's home to 250 restaurants, more than 300 art galleries, at least a hundred boutique shops and a dozen festivals and fairs. Some of the highlights include strolling along Canyon Road and visiting a mile of art galleries. Visit the oldest house in the U.S. and attend mass at the oldest church in the U.S. — the San Miguel Chapel. See over 130,000 folk art objects from more than 100 countries at the Museum of International Folk Art for $12 admission. Check the Santa Fe Tourism Office Calendar for events and festivals, as well as historic walking tours (only $14), cooking classes and more. Don't miss the pulled pork sandwiches at Whole Hog Café (from $3.99) and be sure to sample their six signature sauces. On Saturdays, stop by the Farmer’s Market and try local dishes at food stands. Find winter promo rates at La Posada de Santa Fe, a luxury hotel starting at $99 per night. Fly into Albuquerque and rent a car to drive to Santa Fe (Hertz has deals as low as $13.99 per day), so you can take day trips to Taos and Chimayo or go hiking at Bandelier National Park.
Northern California also has many riches and wonders to offer. Nothing beats the morning mist swathing the Golden Gate Bridge during a San Francisco vacation. Be sure to hike at Batteries to Bluffs Trail and take in the expansive ocean views. If you’re craving sparkling pools, shimmering night skies, and majestic mountain scenery, instead of bay views, spending your vacations in Palm Springs is the way to go. Hollywood’s Waiting Room for Heaven is the ultimate desert playground for people-watching and wandering through art galleries.

Why you should go: Prague is quintessentially European, an architecture junkie’s dream for its lofty spires, stuccoed high ceilings, and Art Nouveau quirks. Sure, it’s touristy -- just try fighting through the selfie sticks on Charles Bridge or not wincing in disgust at Kafka bastardized on T-shirts and coffee mugs -- but this is also a city with plenty of nooks and crannies to escape from the masses, from dimly lit bars, minuscule art galleries, or in some old world cafe.

Vacation rental prices vary as much as hotel prices. Case in point: A search of one-bedroom vacation rentals in Manhattan during September results in options ranging from $60 per night to $2,800 per night. Vacation rentals are ideal for longer stays (seven nights or more). Many vacation rentals require minimum stays, so if you’re hoping for a weekend getaway, you may have to look elsewhere.
Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.
Chosen By: Amie O’Shaughnessy, founder and CEO of Ciao Bambino. After having her son, Amie searched extensively for credible resources to provide family-focused advice, direction and useful accommodation information. She quickly realized that there were no relevant resources available, particularly for a discerning traveler, so she decided to help solve this problem and started Ciao Bambino.
How cheap is it? The UK saying “laters” to the EU may be bad news for Brits, but it’s proving to be great news for travelers. Brexit tied a brick to the already-sinking pound; overall it’s down 30 percent against the dollar since summer of 2014. Airfares, too, have dropped. And the UK is, for the next couple of years at least, formally in Europe -- so super cheap air and train fares that currently operate between the UK and the continent still run post-Brexit, pre-exit. You can be in Paris in 2.5 hours by train. Boom! Take that European trip you’ve been dreaming about since your student days, as it may never be cheaper.
Package vacations are a great choice for effortless traveling, as they are quick and easy to book and ensure that everything will be taken care of for you. For example, if your flight is canceled, it’s the travel provider’s job to find a new flight for you. You can rest easy knowing that your vacation will be stress-free and you are protected in case of changes to your itinerary.